Hellenistic and Roman times (338 B.C. - 330 A.D.)

The Macedonians established an oligarchic system of government in Skiathos and the island remained undisturbed for , many years. Historically, it emerges again from the time of Philip V (238-279 B.C.), the Macedonian king who was, at that time, at war with the Romans.

This was a troubled period for the island, as the surrounding areas became scenes of battle.

When the 2nd Macedonian war began, in 200/199 B.C., Philip ordered Skiathos and Skopelos to be destroyed to prevent their falling into the hands of the enemy fleet and being used against him.

And indeed, in the same year, the Roman fleet, together with that of Attalus I of Pergamum,who was an ally of Rome, arrived on the island, and plundered whatever was left after Philip's raid. Despite the great extent of the destruction, the town quickly recovered and, following Philip's defeat at Kynos Kephales in 197 B.C., democracy was again restored. When the Macedonian Kingdom was overthrown in 168 B.C., the Romans granted a degree of freedom to the Greek cities and states. Finally, however in 146 B.C., the whole of Greece was subjugated by the Romans and Skiathos followed the fate of the rest of the country. In 42 B.C., after the battle of Philippi the victor, Antony, handed over Skiathos along with some other islands to the Athenians, as a token of gratitude for their friendly attitude towards him. Skiathos thus re-established its democratic regime, along with the Athenians, and retained it well into the years following the birth of Christ.